# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2b_14srv257
_database_code_depnum_ccdc_archive 'CCDC 1401917'
_audit_update_record             
;
2015-05-20 deposited with the CCDC.
2015-10-13 downloaded from the CCDC.
;
_audit_creation_date             2014-11-24
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
(S)-methyl 3-fluoro-2-oxopiperidine-3-carboxylate 
;
_chemical_formula_moiety         'C7 H10 F N O3'
_chemical_formula_sum            'C7 H10 F N O3'
_chemical_formula_weight         175.16
_chemical_absolute_configuration ad
_chemical_melting_point          '115-116 C'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   8.5224(4)
_cell_length_b                   10.3050(5)
_cell_length_c                   9.1442(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.3404(11)
_cell_angle_gamma                90.00
_cell_volume                     803.06(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8801
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.47
_cell_measurement_theta_min      4.29
_exptl_absorpt_coefficient_mu    1.105
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1189 before and 0.0931 after correction.
The Ratio of minimum to maximum transmission is 0.8291.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.29
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7399
_diffrn_reflns_theta_full        72.46
_diffrn_reflns_theta_max         72.46
_diffrn_reflns_theta_min         4.84
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  D8Venture
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'ImuS microsource'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                2829
_reflns_number_total             2833
_reflns_threshold_expression     >2sigma(I)
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         2833
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0547
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1520
_refine_ls_wR_factor_ref         0.1520
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
F1 F 0.7533(2) 0.48062(18) 0.3623(2) 0.0362(4) Uani 1 d . . .
O1 O 0.8108(3) 0.7298(2) 0.2396(2) 0.0377(5) Uani 1 d . . .
O2 O 0.6992(2) 0.7552(2) 0.5858(2) 0.0309(5) Uani 1 d . . .
O3 O 0.5292(3) 0.6351(3) 0.4548(3) 0.0516(7) Uani 1 d . . .
N1 N 1.0467(3) 0.6772(3) 0.3379(3) 0.0362(6) Uani 1 d . . .
C1 C 0.8905(4) 0.6734(3) 0.3319(3) 0.0279(6) Uani 1 d . . .
C2 C 0.8069(3) 0.5869(3) 0.4447(3) 0.0299(6) Uani 1 d . . .
C3 C 0.9074(4) 0.5363(4) 0.5693(4) 0.0356(7) Uani 1 d . . .
C4 C 1.0664(4) 0.4980(4) 0.5137(4) 0.0388(7) Uani 1 d . . .
C5 C 1.1465(4) 0.6158(4) 0.4497(4) 0.0445(9) Uani 1 d . . .
C6 C 0.6594(3) 0.6595(3) 0.4946(3) 0.0291(6) Uani 1 d . . .
C7 C 0.5692(4) 0.8382(3) 0.6321(4) 0.0393(8) Uani 1 d . . .
H1 H 1.102(5) 0.712(4) 0.270(5) 0.036(10) Uiso 1 d . . .
H3A H 0.917(5) 0.596(4) 0.629(5) 0.036(10) Uiso 1 d . . .
H3B H 0.852(5) 0.469(5) 0.619(5) 0.050(12) Uiso 1 d . . .
H4A H 1.059(4) 0.425(4) 0.439(4) 0.029(9) Uiso 1 d . . .
H4B H 1.125(6) 0.465(6) 0.575(6) 0.063(14) Uiso 1 d . . .
H5A H 1.180(5) 0.690(4) 0.533(4) 0.038(10) Uiso 1 d . . .
H5B H 1.233(5) 0.590(4) 0.401(4) 0.037(10) Uiso 1 d . . .
H7A H 0.531(5) 0.884(5) 0.545(5) 0.041(10) Uiso 1 d . . .
H7B H 0.482(5) 0.789(4) 0.667(4) 0.037(10) Uiso 1 d . . .
H7C H 0.628(5) 0.898(4) 0.716(5) 0.044(11) Uiso 1 d . . .
F11 F 0.2797(2) 0.66201(19) 0.82147(19) 0.0373(4) Uani 1 d . . .
O11 O 0.2890(3) 0.7040(2) 1.1254(2) 0.0364(5) Uani 1 d . . .
O12 O 0.1743(2) 0.4135(2) 1.0648(2) 0.0332(5) Uani 1 d . . .
O13 O 0.0326(3) 0.5222(2) 0.8952(2) 0.0366(5) Uani 1 d . . .
N11 N 0.5238(3) 0.6050(3) 1.0965(3) 0.0340(6) Uani 1 d . . .
C11 C 0.3759(3) 0.6296(3) 1.0590(3) 0.0284(6) Uani 1 d . . .
C12 C 0.3111(3) 0.5620(3) 0.9204(3) 0.0280(6) Uani 1 d . . .
C13 C 0.4223(4) 0.4644(4) 0.8494(4) 0.0360(7) Uani 1 d . . .
C14 C 0.5908(4) 0.5122(3) 0.8589(3) 0.0353(7) Uani 1 d . . .
C15 C 0.6367(4) 0.5246(4) 1.0182(4) 0.0360(7) Uani 1 d . . .
C16 C 0.1539(4) 0.4991(3) 0.9564(3) 0.0302(6) Uani 1 d . . .
C17 C 0.0352(4) 0.3397(4) 1.1030(4) 0.0389(8) Uani 1 d . . .
H11 H 0.562(5) 0.639(5) 1.183(5) 0.044(11) Uiso 1 d . . .
H13A H 0.424(4) 0.391(4) 0.906(4) 0.029(9) Uiso 1 d . . .
H13B H 0.391(5) 0.445(5) 0.742(5) 0.048(11) Uiso 1 d . . .
H14A H 0.667(5) 0.452(5) 0.816(5) 0.052(12) Uiso 1 d . . .
H14B H 0.607(4) 0.608(3) 0.818(4) 0.022(7) Uiso 1 d . . .
H15A H 0.727(5) 0.567(4) 1.039(4) 0.040(10) Uiso 1 d . . .
H15B H 0.634(4) 0.446(4) 1.062(4) 0.025(8) Uiso 1 d . . .
H17A H -0.054(6) 0.392(6) 1.141(6) 0.062(14) Uiso 1 d . . .
H17B H 0.080(6) 0.274(6) 1.157(6) 0.060(13) Uiso 1 d . . .
H17C H 0.001(6) 0.287(5) 1.026(6) 0.053(13) Uiso 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.404(4) . ?
O1 C1 1.226(4) . ?
O2 C6 1.333(4) . ?
O2 C7 1.465(4) . ?
O3 C6 1.193(4) . ?
N1 C1 1.333(4) . ?
N1 C5 1.469(5) . ?
N1 H1 0.86(5) . ?
C1 C2 1.541(4) . ?
C2 C3 1.514(4) . ?
C2 C6 1.535(4) . ?
C3 C4 1.503(5) . ?
C3 H3A 0.83(5) . ?
C3 H3B 0.95(5) . ?
C4 C5 1.513(6) . ?
C4 H4A 1.02(4) . ?
C4 H4B 0.82(6) . ?
C5 H5A 1.12(4) . ?
C5 H5B 0.91(4) . ?
C7 H7A 0.98(4) . ?
C7 H7B 0.96(4) . ?
C7 H7C 1.11(4) . ?
F11 C12 1.396(3) . ?
O11 C11 1.229(4) . ?
O12 C16 1.337(4) . ?
O12 C17 1.454(4) . ?
O13 C16 1.196(4) . ?
N11 C11 1.328(4) . ?
N11 C15 1.461(4) . ?
N11 H11 0.93(5) . ?
C11 C12 1.546(4) . ?
C12 C13 1.529(4) . ?
C12 C16 1.526(4) . ?
C13 C14 1.521(5) . ?
C13 H13A 0.91(4) . ?
C13 H13B 1.03(5) . ?
C14 C15 1.511(5) . ?
C14 H14A 0.98(5) . ?
C14 H14B 1.06(4) . ?
C15 H15A 0.91(5) . ?
C15 H15B 0.91(4) . ?
C17 H17A 1.00(5) . ?
C17 H17B 0.92(6) . ?
C17 H17C 0.94(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O2 C7 115.0(2) . . ?
C1 N1 C5 126.2(3) . . ?
C1 N1 H1 122(3) . . ?
C5 N1 H1 112(3) . . ?
O1 C1 N1 124.3(3) . . ?
O1 C1 C2 118.6(3) . . ?
N1 C1 C2 117.1(3) . . ?
F1 C2 C1 104.1(2) . . ?
F1 C2 C3 108.4(3) . . ?
F1 C2 C6 106.0(2) . . ?
C3 C2 C1 116.2(3) . . ?
C3 C2 C6 113.8(2) . . ?
C6 C2 C1 107.4(2) . . ?
C2 C3 H3A 107(3) . . ?
C2 C3 H3B 109(3) . . ?
C4 C3 C2 110.1(3) . . ?
C4 C3 H3A 109(3) . . ?
C4 C3 H3B 115(3) . . ?
H3A C3 H3B 106(4) . . ?
C3 C4 C5 109.2(3) . . ?
C3 C4 H4A 111(2) . . ?
C3 C4 H4B 115(4) . . ?
C5 C4 H4A 111(2) . . ?
C5 C4 H4B 109(4) . . ?
H4A C4 H4B 101(4) . . ?
N1 C5 C4 110.8(3) . . ?
N1 C5 H5A 109(2) . . ?
N1 C5 H5B 105(3) . . ?
C4 C5 H5A 114(2) . . ?
C4 C5 H5B 109(3) . . ?
H5A C5 H5B 109(3) . . ?
O2 C6 C2 109.9(2) . . ?
O3 C6 O2 125.4(3) . . ?
O3 C6 C2 124.6(3) . . ?
O2 C7 H7A 107(3) . . ?
O2 C7 H7B 112(3) . . ?
O2 C7 H7C 101(2) . . ?
H7A C7 H7B 106(3) . . ?
H7A C7 H7C 117(3) . . ?
H7B C7 H7C 114(3) . . ?
C16 O12 C17 114.9(2) . . ?
C11 N11 C15 127.4(3) . . ?
C11 N11 H11 119(3) . . ?
C15 N11 H11 114(3) . . ?
O11 C11 N11 124.4(3) . . ?
O11 C11 C12 118.2(3) . . ?
N11 C11 C12 117.4(3) . . ?
F11 C12 C11 105.3(2) . . ?
F11 C12 C13 109.1(2) . . ?
F11 C12 C16 106.7(2) . . ?
C13 C12 C11 115.2(2) . . ?
C16 C12 C11 108.9(2) . . ?
C16 C12 C13 111.1(3) . . ?
C12 C13 H13A 108(2) . . ?
C12 C13 H13B 112(3) . . ?
C14 C13 C12 110.5(3) . . ?
C14 C13 H13A 103(2) . . ?
C14 C13 H13B 111(3) . . ?
H13A C13 H13B 112(3) . . ?
C13 C14 H14A 113(3) . . ?
C13 C14 H14B 113.7(17) . . ?
C15 C14 C13 108.7(3) . . ?
C15 C14 H14A 106(3) . . ?
C15 C14 H14B 103.1(18) . . ?
H14A C14 H14B 111(3) . . ?
N11 C15 C14 110.7(3) . . ?
N11 C15 H15A 101(3) . . ?
N11 C15 H15B 106(2) . . ?
C14 C15 H15A 117(3) . . ?
C14 C15 H15B 110(2) . . ?
H15A C15 H15B 111(4) . . ?
O12 C16 C12 109.2(2) . . ?
O13 C16 O12 125.9(3) . . ?
O13 C16 C12 124.9(3) . . ?
O12 C17 H17A 115(3) . . ?
O12 C17 H17B 100(3) . . ?
O12 C17 H17C 112(3) . . ?
H17A C17 H17B 122(4) . . ?
H17A C17 H17C 110(4) . . ?
H17B C17 H17C 96(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O11 0.86(5) 2.08(4) 2.857(4) 150(4) 1_654
N11 H11 O1 0.93(5) 2.37(4) 3.051(3) 130(3) 1_556

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C2 C3 C4 76.8(3) . . . . ?
F1 C2 C6 O2 174.0(2) . . . . ?
F1 C2 C6 O3 -7.5(4) . . . . ?
O1 C1 C2 F1 69.8(3) . . . . ?
O1 C1 C2 C3 -171.0(3) . . . . ?
O1 C1 C2 C6 -42.3(3) . . . . ?
N1 C1 C2 F1 -107.3(3) . . . . ?
N1 C1 C2 C3 11.9(4) . . . . ?
N1 C1 C2 C6 140.6(3) . . . . ?
C1 N1 C5 C4 27.5(5) . . . . ?
C1 C2 C3 C4 -39.9(4) . . . . ?
C1 C2 C6 O2 -75.3(3) . . . . ?
C1 C2 C6 O3 103.3(4) . . . . ?
C2 C3 C4 C5 61.3(4) . . . . ?
C3 C2 C6 O2 54.9(3) . . . . ?
C3 C2 C6 O3 -126.6(4) . . . . ?
C3 C4 C5 N1 -54.4(4) . . . . ?
C5 N1 C1 O1 177.4(3) . . . . ?
C5 N1 C1 C2 -5.7(5) . . . . ?
C6 C2 C3 C4 -165.5(3) . . . . ?
C7 O2 C6 O3 -3.2(5) . . . . ?
C7 O2 C6 C2 175.4(2) . . . . ?
F11 C12 C13 C14 80.9(3) . . . . ?
F11 C12 C16 O12 -172.2(2) . . . . ?
F11 C12 C16 O13 8.8(4) . . . . ?
O11 C11 C12 F11 63.5(3) . . . . ?
O11 C11 C12 C13 -176.2(3) . . . . ?
O11 C11 C12 C16 -50.7(4) . . . . ?
N11 C11 C12 F11 -115.2(3) . . . . ?
N11 C11 C12 C13 5.1(4) . . . . ?
N11 C11 C12 C16 130.6(3) . . . . ?
C11 N11 C15 C14 22.3(5) . . . . ?
C11 C12 C13 C14 -37.3(4) . . . . ?
C11 C12 C16 O12 -58.9(3) . . . . ?
C11 C12 C16 O13 122.0(3) . . . . ?
C12 C13 C14 C15 61.8(4) . . . . ?
C13 C12 C16 O12 69.0(3) . . . . ?
C13 C12 C16 O13 -110.1(4) . . . . ?
C13 C14 C15 N11 -53.6(4) . . . . ?
C15 N11 C11 O11 -175.8(3) . . . . ?
C15 N11 C11 C12 2.8(5) . . . . ?
C16 C12 C13 C14 -161.7(3) . . . . ?
C17 O12 C16 O13 3.2(5) . . . . ?
C17 O12 C16 C12 -175.8(3) . . . . ?

_iucr_refinement_instructions_details 
;
TITL 14srv257 in P21 #4
REM reset to P21 #4
CELL 1.54178 8.5224 10.305 9.1442 90 90.3404 90
ZERR 4 0.0004 0.0005 0.0004 0 0.0011 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H F N O
UNIT 28 40 4 4 12
EQIV $1 1+X,+Y,-1+Z
EQIV $2 +X,+Y,1+Z

L.S. 9
PLAN  5
TEMP -153.15
HTAB N1 O11_$1
HTAB N11 O1_$2
BOND $h
CONF 
fmap 2 53
acta 
OMIT -2 145
OMIT 2 0 9
OMIT 1 0 1
OMIT 0 2 9
OMIT 2 3 9
WGHT 0.1 0.5
FVAR 0.38693
REM <olex2.extras>
REM <HklSrc "%D:\\Struc\\14S\\14srv257\\14srv257.hkl">
REM </olex2.extras>

F1    3     0.75331  0.48062  0.36230  11.00000  0.03532  0.03303  0.04028 =
 -0.00847  0.00420 -0.00485 
O1    5     0.81082  0.72976  0.23958  11.00000  0.03730  0.03909  0.03655 =
 0.00581 -0.00526  0.00017 
O2    5     0.69916  0.75516  0.58583  11.00000  0.02595  0.02860  0.03824 =
 -0.00364  0.00308  0.00104 
O3    5     0.52916  0.63509  0.45480  11.00000  0.02792  0.06012  0.06666 =
 -0.02801 -0.00173  0.00253 
N1    4     1.04671  0.67724  0.33792  11.00000  0.02990  0.04413  0.03447 =
 0.00317  0.00428 -0.00342 
C1    1     0.89047  0.67344  0.33192  11.00000  0.02941  0.02694  0.02725 =
 -0.00340 -0.00008  0.00198 
C2    1     0.80691  0.58688  0.44466  11.00000  0.02869  0.02982  0.03106 =
 -0.00224 -0.00027  0.00138 
C3    1     0.90740  0.53632  0.56934  11.00000  0.03950  0.03488  0.03250 =
 0.00070  0.00125  0.00947 
C4    1     1.06641  0.49795  0.51375  11.00000  0.03821  0.04401  0.03403 =
 0.00166 -0.00273  0.01403 
C5    1     1.14650  0.61581  0.44968  11.00000  0.02478  0.06330  0.04545 =
 -0.00044 -0.00691  0.00128 
C6    1     0.65938  0.65954  0.49463  11.00000  0.02403  0.02974  0.03352 =
 0.00233  0.00119 -0.00365 
C7    1     0.56917  0.83824  0.63209  11.00000  0.03527  0.03405  0.04855 =
 -0.00391  0.00829  0.00512 
H1    2     1.10179  0.71243  0.26997  11.00000  0.03598 
H3a   2     0.91723  0.59641  0.62930  11.00000  0.03641 
H3b   2     0.85209  0.46909  0.61893  11.00000  0.05003 
H4a   2     1.05865  0.42453  0.43872  11.00000  0.02887 
H4b   2     1.12505  0.46481  0.57528  11.00000  0.06294 
H5a   2     1.18006  0.69004  0.53304  11.00000  0.03772 
H5b   2     1.23336  0.59025  0.40058  11.00000  0.03699 
H7a   2     0.53057  0.88371  0.54476  11.00000  0.04055 
H7b   2     0.48197  0.78888  0.66711  11.00000  0.03686 
H7c   2     0.62802  0.89823  0.71646  11.00000  0.04414 

F11   3     0.27969  0.66201  0.82147  11.00000  0.03754  0.04151  0.03290 =
 0.00844 -0.00101 -0.00280 
O11   5     0.28904  0.70404  1.12544  11.00000  0.03413  0.03731  0.03774 =
 -0.00515  0.00402  0.00030 
O12   5     0.17430  0.41350  1.06477  11.00000  0.02990  0.03616  0.03366 =
 0.00680 -0.00187 -0.00330 
O13   5     0.03261  0.52221  0.89522  11.00000  0.02810  0.04491  0.03676 =
 0.00355 -0.00226  0.00007 
N11   4     0.52375  0.60498  1.09655  11.00000  0.03077  0.03767  0.03339 =
 -0.00438 -0.00316  0.00288 
C11   1     0.37594  0.62960  1.05898  11.00000  0.02879  0.02730  0.02911 =
 0.00167  0.00388 -0.00327 
C12   1     0.31112  0.56198  0.92037  11.00000  0.02527  0.03007  0.02878 =
 0.00339  0.00057  0.00077 
C13   1     0.42230  0.46437  0.84944  11.00000  0.03438  0.04158  0.03217 =
 -0.00507  0.00129  0.00151 
C14   1     0.59084  0.51224  0.85893  11.00000  0.03087  0.03863  0.03661 =
 0.00222  0.00668  0.00362 
C15   1     0.63666  0.52458  1.01821  11.00000  0.02890  0.03741  0.04180 =
 0.00143 -0.00111  0.00387 
C16   1     0.15391  0.49909  0.95638  11.00000  0.03191  0.02891  0.02985 =
 -0.00083 -0.00038 -0.00139 
C17   1     0.03515  0.33965  1.10303  11.00000  0.03789  0.03700  0.04180 =
 0.00727 -0.00018 -0.00901 
H11   2     0.56242  0.63943  1.18334  11.00000  0.04408 
H13a  2     0.42425  0.39146  0.90602  11.00000  0.02924 
H13b  2     0.39140  0.44476  0.74233  11.00000  0.04822 
H14a  2     0.66664  0.45151  0.81573  11.00000  0.05244 
H14b  2     0.60653  0.60752  0.81844  11.00000  0.02163 
H15a  2     0.72722  0.56680  1.03941  11.00000  0.04025 
H15b  2     0.63419  0.44590  1.06248  11.00000  0.02455 
H17a  2    -0.05407  0.39239  1.14136  11.00000  0.06207 
H17b  2     0.08033  0.27428  1.15700  11.00000  0.05966 
H17c  2     0.00050  0.28659  1.02560  11.00000  0.05256 
HKLF 4

END
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2c_14srv258
_database_code_depnum_ccdc_archive 'CCDC 1401918'
_audit_update_record             
;
2015-05-20 deposited with the CCDC.
2015-10-13 downloaded from the CCDC.
;
_audit_creation_date             2014-11-24
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
(R)-methyl 3-fluoro-2-oxopiperidine-3-carboxylate  
;
_chemical_formula_moiety         'C7 H10 F N O3'
_chemical_formula_sum            'C7 H10 F N O3'
_chemical_formula_weight         175.16
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   8.5211(3)
_cell_length_b                   10.3039(3)
_cell_length_c                   9.1547(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.3650(8)
_cell_angle_gamma                90.00
_cell_volume                     803.77(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7543
_cell_measurement_temperature    120.0(2)
_cell_measurement_theta_max      74.36
_cell_measurement_theta_min      4.29
_exptl_absorpt_coefficient_mu    1.104
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8531
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1118 before and 0.0883 after correction.
The Ratio of minimum to maximum transmission is 0.8531.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.24
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6957
_diffrn_reflns_theta_full        72.47
_diffrn_reflns_theta_max         72.47
_diffrn_reflns_theta_min         4.83
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  '3-circle diffractometer'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'ImuS microsource'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                2893
_reflns_number_total             2916
_reflns_threshold_expression     >2sigma(I)
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(16)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         2916
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0513
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.1200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1451
_refine_ls_wR_factor_ref         0.1455
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
F1 F 0.74634(17) 0.54728(15) 0.13756(16) 0.0368(4) Uani 1 d . . .
O1 O 0.6903(2) 0.29830(19) 0.2600(2) 0.0373(4) Uani 1 d . . .
O2 O 0.80105(19) 0.27347(17) -0.08541(19) 0.0311(4) Uani 1 d . . .
O3 O 0.9704(2) 0.3938(3) 0.0451(3) 0.0528(6) Uani 1 d . . .
N1 N 0.4532(3) 0.3510(2) 0.1621(2) 0.0358(5) Uani 1 d . . .
C1 C 0.6094(3) 0.3546(2) 0.1680(2) 0.0286(5) Uani 1 d . . .
C2 C 0.6929(3) 0.4414(2) 0.0549(3) 0.0290(5) Uani 1 d . . .
C3 C 0.5934(3) 0.4920(3) -0.0694(3) 0.0346(6) Uani 1 d . . .
C4 C 0.4317(3) 0.5305(3) -0.0134(3) 0.0379(6) Uani 1 d . . .
C5 C 0.3524(3) 0.4125(3) 0.0507(3) 0.0440(7) Uani 1 d . . .
C6 C 0.8403(3) 0.3682(2) 0.0053(3) 0.0299(5) Uani 1 d . . .
C7 C 0.9305(3) 0.1902(3) -0.1316(3) 0.0396(6) Uani 1 d . . .
H1 H 0.411(4) 0.319(4) 0.234(4) 0.036(8) Uiso 1 d . . .
H3A H 0.582(5) 0.432(4) -0.137(4) 0.052(10) Uiso 1 d . . .
H3B H 0.650(5) 0.563(4) -0.117(4) 0.051(10) Uiso 1 d . . .
H4A H 0.444(4) 0.599(3) 0.055(4) 0.031(7) Uiso 1 d . . .
H4B H 0.371(3) 0.560(3) -0.097(3) 0.019(6) Uiso 1 d . . .
H5A H 0.263(4) 0.444(4) 0.098(4) 0.038(8) Uiso 1 d . . .
H5B H 0.321(4) 0.344(4) -0.037(4) 0.046(9) Uiso 1 d . . .
H7A H 0.874(4) 0.137(3) -0.217(4) 0.035(8) Uiso 1 d . . .
H7B H 0.961(5) 0.139(5) -0.055(5) 0.056(11) Uiso 1 d . . .
H7C H 1.001(5) 0.244(4) -0.177(4) 0.047(9) Uiso 1 d . . .
F11 F 0.21984(18) 0.36622(16) 0.67839(16) 0.0375(4) Uani 1 d . . .
O11 O 0.2110(2) 0.32427(19) 0.3745(2) 0.0360(4) Uani 1 d . . .
O12 O 0.3261(2) 0.61490(19) 0.43529(19) 0.0342(4) Uani 1 d . . .
O13 O 0.4675(2) 0.50597(19) 0.6046(2) 0.0355(4) Uani 1 d . . .
N11 N -0.0241(2) 0.4225(2) 0.4037(2) 0.0338(5) Uani 1 d . . .
C11 C 0.1242(3) 0.3988(2) 0.4416(3) 0.0298(5) Uani 1 d . . .
C12 C 0.1891(3) 0.4664(2) 0.5796(3) 0.0289(5) Uani 1 d . . .
C13 C 0.0769(3) 0.5633(3) 0.6508(3) 0.0354(5) Uani 1 d . . .
C14 C -0.0918(3) 0.5154(3) 0.6408(3) 0.0354(5) Uani 1 d . . .
C15 C -0.1381(3) 0.5033(3) 0.4817(3) 0.0361(6) Uani 1 d . . .
C16 C 0.3466(3) 0.5293(2) 0.5431(2) 0.0297(5) Uani 1 d . . .
C17 C 0.4646(3) 0.6888(3) 0.3979(3) 0.0391(6) Uani 1 d . . .
H11 H -0.057(4) 0.396(4) 0.329(4) 0.045(9) Uiso 1 d . . .
H13A H 0.095(4) 0.647(4) 0.600(4) 0.036(8) Uiso 1 d . . .
H13B H 0.104(5) 0.584(4) 0.749(5) 0.057(11) Uiso 1 d . . .
H14A H -0.170(4) 0.576(4) 0.692(4) 0.040(8) Uiso 1 d . . .
H14B H -0.101(4) 0.433(4) 0.687(4) 0.038(8) Uiso 1 d . . .
H15A H -0.141(3) 0.591(3) 0.438(3) 0.019(6) Uiso 1 d . . .
H15B H -0.231(4) 0.461(4) 0.473(4) 0.037(8) Uiso 1 d . . .
H17A H 0.422(4) 0.742(5) 0.328(4) 0.050(10) Uiso 1 d . . .
H17B H 0.544(6) 0.625(6) 0.345(6) 0.083(15) Uiso 1 d . . .
H17C H 0.502(4) 0.726(4) 0.472(4) 0.039(9) Uiso 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.402(3) . ?
O1 C1 1.230(3) . ?
O2 C6 1.323(3) . ?
O2 C7 1.462(3) . ?
O3 C6 1.195(3) . ?
N1 C1 1.332(3) . ?
N1 C5 1.472(4) . ?
N1 H1 0.82(4) . ?
C1 C2 1.545(3) . ?
C2 C3 1.507(3) . ?
C2 C6 1.536(3) . ?
C3 C4 1.525(4) . ?
C3 H3A 0.88(4) . ?
C3 H3B 0.98(4) . ?
C4 C5 1.512(4) . ?
C4 H4A 0.95(4) . ?
C4 H4B 0.97(3) . ?
C5 H5A 0.94(4) . ?
C5 H5B 1.10(4) . ?
C7 H7A 1.07(3) . ?
C7 H7B 0.91(4) . ?
C7 H7C 0.91(4) . ?
F11 C12 1.396(3) . ?
O11 C11 1.234(3) . ?
O12 C16 1.334(3) . ?
O12 C17 1.447(3) . ?
O13 C16 1.195(3) . ?
N11 C11 1.331(3) . ?
N11 C15 1.468(3) . ?
N11 H11 0.79(4) . ?
C11 C12 1.542(3) . ?
C12 C13 1.530(3) . ?
C12 C16 1.529(3) . ?
C13 C14 1.522(4) . ?
C13 H13A 0.99(4) . ?
C13 H13B 0.95(4) . ?
C14 C15 1.512(4) . ?
C14 H14A 1.03(4) . ?
C14 H14B 0.95(4) . ?
C15 H15A 0.99(3) . ?
C15 H15B 0.91(4) . ?
C17 H17A 0.92(4) . ?
C17 H17B 1.06(6) . ?
C17 H17C 0.84(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O2 C7 115.23(19) . . ?
C1 N1 C5 126.5(2) . . ?
C1 N1 H1 115(2) . . ?
C5 N1 H1 118(2) . . ?
O1 C1 N1 124.8(2) . . ?
O1 C1 C2 118.3(2) . . ?
N1 C1 C2 116.9(2) . . ?
F1 C2 C1 103.74(18) . . ?
F1 C2 C3 108.5(2) . . ?
F1 C2 C6 106.14(18) . . ?
C3 C2 C1 116.5(2) . . ?
C3 C2 C6 113.84(19) . . ?
C6 C2 C1 107.14(19) . . ?
C2 C3 C4 109.9(2) . . ?
C2 C3 H3A 110(3) . . ?
C2 C3 H3B 109(2) . . ?
C4 C3 H3A 109(3) . . ?
C4 C3 H3B 114(2) . . ?
H3A C3 H3B 105(3) . . ?
C3 C4 H4A 108.7(19) . . ?
C3 C4 H4B 106.9(16) . . ?
C5 C4 C3 109.2(2) . . ?
C5 C4 H4A 113(2) . . ?
C5 C4 H4B 108.7(17) . . ?
H4A C4 H4B 110(3) . . ?
N1 C5 C4 110.7(2) . . ?
N1 C5 H5A 108(2) . . ?
N1 C5 H5B 112(2) . . ?
C4 C5 H5A 105(2) . . ?
C4 C5 H5B 110(2) . . ?
H5A C5 H5B 111(3) . . ?
O2 C6 C2 110.10(19) . . ?
O3 C6 O2 125.8(2) . . ?
O3 C6 C2 124.1(2) . . ?
O2 C7 H7A 100.1(18) . . ?
O2 C7 H7B 109(3) . . ?
O2 C7 H7C 106(3) . . ?
H7A C7 H7B 113(3) . . ?
H7A C7 H7C 106(3) . . ?
H7B C7 H7C 121(3) . . ?
C16 O12 C17 114.81(19) . . ?
C11 N11 C15 127.4(2) . . ?
C11 N11 H11 120(3) . . ?
C15 N11 H11 113(3) . . ?
O11 C11 N11 123.7(2) . . ?
O11 C11 C12 118.5(2) . . ?
N11 C11 C12 117.8(2) . . ?
F11 C12 C11 105.15(19) . . ?
F11 C12 C13 108.76(19) . . ?
F11 C12 C16 107.08(18) . . ?
C13 C12 C11 114.9(2) . . ?
C16 C12 C11 108.84(19) . . ?
C16 C12 C13 111.6(2) . . ?
C12 C13 H13A 106(2) . . ?
C12 C13 H13B 113(3) . . ?
C14 C13 C12 110.8(2) . . ?
C14 C13 H13A 113.6(19) . . ?
C14 C13 H13B 111(3) . . ?
H13A C13 H13B 102(3) . . ?
C13 C14 H14A 113(2) . . ?
C13 C14 H14B 110(2) . . ?
C15 C14 C13 109.0(2) . . ?
C15 C14 H14A 108.7(19) . . ?
C15 C14 H14B 110(2) . . ?
H14A C14 H14B 107(3) . . ?
N11 C15 C14 110.3(2) . . ?
N11 C15 H15A 109.5(17) . . ?
N11 C15 H15B 106(2) . . ?
C14 C15 H15A 108.7(16) . . ?
C14 C15 H15B 110(2) . . ?
H15A C15 H15B 112(3) . . ?
O12 C16 C12 109.32(19) . . ?
O13 C16 O12 126.1(2) . . ?
O13 C16 C12 124.5(2) . . ?
O12 C17 H17A 99(2) . . ?
O12 C17 H17B 108(3) . . ?
O12 C17 H17C 110(3) . . ?
H17A C17 H17B 108(4) . . ?
H17A C17 H17C 116(4) . . ?
H17B C17 H17C 115(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O11 0.82(4) 2.14(4) 2.858(3) 145(3) .
N11 H11 O1 0.79(4) 2.46(4) 3.042(3) 132(3) 1_455

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C2 C3 C4 -77.0(3) . . . . ?
F1 C2 C6 O2 -174.02(19) . . . . ?
F1 C2 C6 O3 6.6(3) . . . . ?
O1 C1 C2 F1 -69.9(3) . . . . ?
O1 C1 C2 C3 170.9(2) . . . . ?
O1 C1 C2 C6 42.1(3) . . . . ?
N1 C1 C2 F1 107.3(2) . . . . ?
N1 C1 C2 C3 -11.9(3) . . . . ?
N1 C1 C2 C6 -140.7(2) . . . . ?
C1 N1 C5 C4 -27.6(4) . . . . ?
C1 C2 C3 C4 39.6(3) . . . . ?
C1 C2 C6 O2 75.6(2) . . . . ?
C1 C2 C6 O3 -103.8(3) . . . . ?
C2 C3 C4 C5 -60.9(3) . . . . ?
C3 C2 C6 O2 -54.7(3) . . . . ?
C3 C2 C6 O3 125.9(3) . . . . ?
C3 C4 C5 N1 54.0(3) . . . . ?
C5 N1 C1 O1 -177.3(3) . . . . ?
C5 N1 C1 C2 5.7(4) . . . . ?
C6 C2 C3 C4 165.1(2) . . . . ?
C7 O2 C6 O3 3.9(4) . . . . ?
C7 O2 C6 C2 -175.51(19) . . . . ?
F11 C12 C13 C14 -80.8(2) . . . . ?
F11 C12 C16 O12 172.25(19) . . . . ?
F11 C12 C16 O13 -9.0(3) . . . . ?
O11 C11 C12 F11 -63.9(3) . . . . ?
O11 C11 C12 C13 176.5(2) . . . . ?
O11 C11 C12 C16 50.5(3) . . . . ?
N11 C11 C12 F11 114.7(2) . . . . ?
N11 C11 C12 C13 -4.9(3) . . . . ?
N11 C11 C12 C16 -130.9(2) . . . . ?
C11 N11 C15 C14 -22.7(4) . . . . ?
C11 C12 C13 C14 36.7(3) . . . . ?
C11 C12 C16 O12 59.1(3) . . . . ?
C11 C12 C16 O13 -122.2(3) . . . . ?
C12 C13 C14 C15 -61.7(3) . . . . ?
C13 C12 C16 O12 -68.8(2) . . . . ?
C13 C12 C16 O13 109.9(3) . . . . ?
C13 C14 C15 N11 53.6(3) . . . . ?
C15 N11 C11 O11 176.1(2) . . . . ?
C15 N11 C11 C12 -2.4(4) . . . . ?
C16 C12 C13 C14 161.3(2) . . . . ?
C17 O12 C16 O13 -3.3(4) . . . . ?
C17 O12 C16 C12 175.4(2) . . . . ?

_iucr_refinement_instructions_details 
;
TITL 14srv258 in P21 #4
REM reset to P21 #4
CELL 1.54178 8.5211 10.3039 9.1547 90 90.365 90
ZERR 4 0.0003 0.0003 0.0003 0 0.0008 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H F N O
UNIT 28 40 4 4 12
EQIV $1 -1+X,+Y,+Z

L.S. 9 0 0
PLAN  5
TEMP -273.15
HTAB N1 O11
HTAB N11 O1_$1
CONF 
BOND $h
fmap 2 53
acta 
OMIT -2 145
WGHT 0.1 0.12
FVAR 0.32691
REM <olex2.extras>
REM <HklSrc "%D:\\Struc\\14S\\14srv258\\14srv258.hkl">
REM </olex2.extras>

F1    3     0.74634  0.54728  0.13756  11.00000  0.03657  0.03319  0.04063 =
 -0.00886  0.00444 -0.00345 
O1    5     0.69026  0.29830  0.26000  11.00000  0.03638  0.03953  0.03590 =
 0.00500 -0.00473  0.00110 
O2    5     0.80105  0.27347 -0.08541  11.00000  0.02611  0.02855  0.03881 =
 -0.00280  0.00273  0.00224 
O3    5     0.97044  0.39383  0.04513  11.00000  0.02519  0.06207  0.07111 =
 -0.02771 -0.00600  0.00258 
N1    4     0.45321  0.35103  0.16206  11.00000  0.02801  0.04359  0.03576 =
 0.00393  0.00189 -0.00022 
C1    1     0.60936  0.35463  0.16801  11.00000  0.02928  0.02974  0.02689 =
 -0.00240 -0.00184  0.00140 
C2    1     0.69287  0.44142  0.05486  11.00000  0.02674  0.02950  0.03079 =
 -0.00137 -0.00012  0.00115 
C3    1     0.59337  0.49201 -0.06939  11.00000  0.03385  0.03905  0.03079 =
 0.00082  0.00136  0.01040 
C4    1     0.43174  0.53049 -0.01338  11.00000  0.03475  0.04373  0.03520 =
 0.00062 -0.00275  0.01250 
C5    1     0.35235  0.41247  0.05067  11.00000  0.02240  0.06002  0.04949 =
 0.00097 -0.00631  0.00303 
C6    1     0.84030  0.36820  0.00531  11.00000  0.02155  0.03252  0.03558 =
 0.00189  0.00104 -0.00035 
C7    1     0.93047  0.19021 -0.13157  11.00000  0.03465  0.03440  0.04991 =
 -0.00385  0.00774  0.00739 
H1    2     0.41121  0.31873  0.23392  11.00000  0.03550 
H3a   2     0.58228  0.43172 -0.13685  11.00000  0.05217 
H3b   2     0.64987  0.56327 -0.11740  11.00000  0.05110 
H4a   2     0.44389  0.59910  0.05549  11.00000  0.03099 
H4b   2     0.37150  0.55964 -0.09690  11.00000  0.01904 
H5a   2     0.26277  0.44405  0.09775  11.00000  0.03791 
H5b   2     0.32084  0.34387 -0.03703  11.00000  0.04606 
H7a   2     0.87360  0.13662 -0.21673  11.00000  0.03493 
H7b   2     0.96120  0.13935 -0.05484  11.00000  0.05647 
H7c   2     1.00056  0.24384 -0.17672  11.00000  0.04654 

F11   3     0.21984  0.36622  0.67839  11.00000  0.03757  0.04085  0.03416 =
 0.01025 -0.00123 -0.00153 
O11   5     0.21100  0.32427  0.37446  11.00000  0.03385  0.03637  0.03791 =
 -0.00462  0.00451  0.00154 
O12   5     0.32612  0.61490  0.43529  11.00000  0.03169  0.03701  0.03392 =
 0.00672 -0.00333 -0.00450 
O13   5     0.46753  0.50597  0.60458  11.00000  0.02916  0.03999  0.03741 =
 0.00418 -0.00281 -0.00127 
N11   4    -0.02409  0.42253  0.40367  11.00000  0.03042  0.03714  0.03376 =
 -0.00302 -0.00520  0.00094 
C11   1     0.12419  0.39885  0.44162  11.00000  0.03003  0.02793  0.03146 =
 0.00163  0.00181 -0.00388 
C12   1     0.18912  0.46644  0.57964  11.00000  0.02852  0.02949  0.02857 =
 0.00264 -0.00231  0.00053 
C13   1     0.07692  0.56326  0.65082  11.00000  0.03185  0.04057  0.03381 =
 -0.00692  0.00168 -0.00104 
C14   1    -0.09182  0.51538  0.64081  11.00000  0.03066  0.03905  0.03654 =
 0.00322  0.00406  0.00381 
C15   1    -0.13808  0.50331  0.48168  11.00000  0.02947  0.03956  0.03933 =
 0.00032 -0.00298  0.00302 
C16   1     0.34661  0.52931  0.54313  11.00000  0.03097  0.02943  0.02867 =
 -0.00237 -0.00258 -0.00130 
C17   1     0.46460  0.68878  0.39790  11.00000  0.03977  0.03850  0.03908 =
 0.00631 -0.00152 -0.01185 
H11   2    -0.05711  0.39614  0.32857  11.00000  0.04483 
H13a  2     0.09467  0.64659  0.60021  11.00000  0.03580 
H13b  2     0.10450  0.58367  0.74876  11.00000  0.05659 
H14a  2    -0.17022  0.57643  0.69180  11.00000  0.03951 
H14b  2    -0.10053  0.43282  0.68723  11.00000  0.03847 
H15a  2    -0.14052  0.59087  0.43794  11.00000  0.01891 
H15b  2    -0.23148  0.46139  0.47291  11.00000  0.03685 
H17a  2     0.42194  0.74213  0.32813  11.00000  0.04960 
H17b  2     0.54419  0.62482  0.34490  11.00000  0.08319 
H17c  2     0.50153  0.72614  0.47249  11.00000  0.03870 
HKLF 4

END
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4c_15srv065
_database_code_depnum_ccdc_archive 'CCDC 1401919'
_audit_update_record             
;
2015-05-20 deposited with the CCDC.
2015-10-13 downloaded from the CCDC.
;
_audit_creation_date             2015-03-13
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 dimethyl (2-aminopropyl)fluoromalonate hydrochloride 
;
_chemical_formula_moiety         'Cl, C8 H15 F N O4'
_chemical_formula_sum            'C8 H15 Cl F N O4'
_chemical_formula_weight         243.66
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H15 Cl1 F1 N1 O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   5.8210(4)
_cell_length_b                   6.4875(5)
_cell_length_c                   15.7485(12)
_cell_angle_alpha                100.738(7)
_cell_angle_beta                 96.625(6)
_cell_angle_gamma                94.612(6)
_cell_volume                     577.23(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3123
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      32.2490
_cell_measurement_theta_min      3.2000
_exptl_absorpt_coefficient_mu    0.340
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8623
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.66
_diffrn_ambient_temperature      120.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -37.00   37.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  -57.0000  120.0000 74

#__ type_ start__ end____ width___ exp.time_
  2 omega   -1.00   75.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -112.0000   83.0000 76

#__ type_ start__ end____ width___ exp.time_
  3 omega   -1.00   98.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   77.0000  -30.0000 99

#__ type_ start__ end____ width___ exp.time_
  4 omega  -19.00    7.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -100.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   21.00   71.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -100.0000 -150.0000 50

#__ type_ start__ end____ width___ exp.time_
  6 omega  -12.00  102.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   19.0000  -60.0000 114

#__ type_ start__ end____ width___ exp.time_
  7 omega -104.00  -35.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337 -178.0000 -150.0000 69

#__ type_ start__ end____ width___ exp.time_
  8 omega  -97.00   -7.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337  -57.0000   30.0000 90

#__ type_ start__ end____ width___ exp.time_
  9 omega   -1.00   38.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   77.0000 -150.0000 39

#__ type_ start__ end____ width___ exp.time_
 10 omega    3.00  101.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   38.0000  150.0000 98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ω-scan
_diffrn_orient_matrix_UB_11      0.0842586000
_diffrn_orient_matrix_UB_12      0.0045224000
_diffrn_orient_matrix_UB_13      -0.0289226000
_diffrn_orient_matrix_UB_21      0.0897726000
_diffrn_orient_matrix_UB_22      0.0025254000
_diffrn_orient_matrix_UB_23      0.0348143000
_diffrn_orient_matrix_UB_31      -0.0074563000
_diffrn_orient_matrix_UB_32      -0.1117729000
_diffrn_orient_matrix_UB_33      -0.0095307000
_diffrn_radiation_collimation    monochromator
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2374
_reflns_number_total             2785
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2785
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0521
_refine_ls_restrained_S_all      1.165
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0350P)²+0.8000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1289
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1D,H1E), C2(H2A,H2B), C3(H3A,H3B)
2.b Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C6(H6A,H6B,H6C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.75418(10) 1.29673(9) 0.51960(4) 0.02011(16) Uani 1 d . . .
F1 F 0.6831(3) 0.9887(2) 0.17917(10) 0.0248(4) Uani 1 d . . .
O1 O 0.5595(4) 0.7691(4) 0.01629(14) 0.0353(5) Uani 1 d . . .
O2 O 0.1871(3) 0.7620(3) 0.04072(12) 0.0256(4) Uani 1 d . . .
O3 O 0.3597(3) 0.5205(3) 0.19529(13) 0.0273(4) Uani 1 d . . .
O4 O 0.7177(3) 0.6800(3) 0.24970(13) 0.0286(5) Uani 1 d . . .
N1 N 0.2217(4) 1.1772(3) 0.44695(14) 0.0195(4) Uani 1 d . . .
H1A H 0.2229 1.0478 0.4613 0.023 Uiso 1 calc . . GR
H1B H 0.1086 1.2461 0.4719 0.023 Uiso 1 calc . . GR
H1C H 0.3623 1.2530 0.4666 0.023 Uiso 1 calc . . GR
C1 C 0.1745(5) 1.1523(4) 0.35047(17) 0.0227(5) Uani 1 d . . .
H1D H 0.1831 1.2930 0.3345 0.027 Uiso 1 calc . . R
H1E H 0.0157 1.0812 0.3295 0.027 Uiso 1 calc . . R
C2 C 0.3501(4) 1.0233(4) 0.30724(17) 0.0203(5) Uani 1 d . . .
H2A H 0.3518 0.8882 0.3278 0.024 Uiso 1 calc . . R
H2B H 0.5072 1.1009 0.3242 0.024 Uiso 1 calc . . R
C3 C 0.2916(5) 0.9785(4) 0.20797(17) 0.0206(5) Uani 1 d . . .
H3A H 0.1380 0.8946 0.1910 0.025 Uiso 1 calc . . R
H3B H 0.2815 1.1136 0.1878 0.025 Uiso 1 calc . . R
C4 C 0.4737(4) 0.8589(4) 0.16362(17) 0.0188(5) Uani 1 d . . .
C5 C 0.4151(5) 0.7910(4) 0.06354(17) 0.0215(5) Uani 1 d . . .
C6 C 0.1074(6) 0.6948(5) -0.05202(18) 0.0320(7) Uani 1 d . . .
H6A H 0.1722 0.7978 -0.0835 0.048 Uiso 1 calc . . GR
H6B H -0.0628 0.6848 -0.0620 0.048 Uiso 1 calc . . GR
H6C H 0.1590 0.5566 -0.0731 0.048 Uiso 1 calc . . GR
C7 C 0.5104(4) 0.6631(4) 0.20300(16) 0.0196(5) Uani 1 d . . .
C8 C 0.7546(7) 0.5106(5) 0.2970(2) 0.0450(9) Uani 1 d . . .
H8A H 0.7465 0.3767 0.2554 0.068 Uiso 1 calc . . GR
H8B H 0.6342 0.5019 0.3352 0.068 Uiso 1 calc . . GR
H8C H 0.9080 0.5391 0.3322 0.068 Uiso 1 calc . . GR


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C4 1.394(3) . ?
O1 C5 1.185(3) . ?
O2 C5 1.323(3) . ?
O2 C6 1.453(3) . ?
O3 C7 1.202(3) . ?
O4 C7 1.324(3) . ?
O4 C8 1.454(3) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C1 1.488(3) . ?
C1 H1D 0.9900 . ?
C1 H1E 0.9900 . ?
C1 C2 1.515(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.528(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.521(4) . ?
C4 C5 1.545(4) . ?
C4 C7 1.533(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O2 C6 116.1(2) . . ?
C7 O4 C8 114.7(2) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
N1 C1 H1D 109.6 . . ?
N1 C1 H1E 109.6 . . ?
N1 C1 C2 110.3(2) . . ?
H1D C1 H1E 108.1 . . ?
C2 C1 H1D 109.6 . . ?
C2 C1 H1E 109.6 . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C1 C2 C3 111.2(2) . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 C2 111.7(2) . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
F1 C4 C3 108.8(2) . . ?
F1 C4 C5 106.4(2) . . ?
F1 C4 C7 108.5(2) . . ?
C3 C4 C5 114.6(2) . . ?
C3 C4 C7 109.2(2) . . ?
C7 C4 C5 109.1(2) . . ?
O1 C5 O2 126.8(3) . . ?
O1 C5 C4 122.9(3) . . ?
O2 C5 C4 110.3(2) . . ?
O2 C6 H6A 109.5 . . ?
O2 C6 H6B 109.5 . . ?
O2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O3 C7 O4 125.8(2) . . ?
O3 C7 C4 122.2(2) . . ?
O4 C7 C4 111.8(2) . . ?
O4 C8 H8A 109.5 . . ?
O4 C8 H8B 109.5 . . ?
O4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A Cl1 0.91 2.32 3.226(2) 172.2 2_676
N1 H1B Cl1 0.91 2.30 3.169(2) 158.9 1_455
N1 H1C Cl1 0.91 2.31 3.160(2) 154.7 .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C4 C5 O1 31.3(3) . . . . ?
F1 C4 C5 O2 -148.9(2) . . . . ?
F1 C4 C7 O3 -176.5(2) . . . . ?
F1 C4 C7 O4 7.7(3) . . . . ?
N1 C1 C2 C3 174.8(2) . . . . ?
C1 C2 C3 C4 177.0(2) . . . . ?
C2 C3 C4 F1 -66.2(3) . . . . ?
C2 C3 C4 C5 174.9(2) . . . . ?
C2 C3 C4 C7 52.2(3) . . . . ?
C3 C4 C5 O1 151.6(3) . . . . ?
C3 C4 C5 O2 -28.6(3) . . . . ?
C3 C4 C7 O3 65.0(3) . . . . ?
C3 C4 C7 O4 -110.8(2) . . . . ?
C5 C4 C7 O3 -60.9(3) . . . . ?
C5 C4 C7 O4 123.2(2) . . . . ?
C6 O2 C5 O1 0.5(4) . . . . ?
C6 O2 C5 C4 -179.3(2) . . . . ?
C7 C4 C5 O1 -85.7(3) . . . . ?
C7 C4 C5 O2 94.1(2) . . . . ?
C8 O4 C7 O3 -2.2(4) . . . . ?
C8 O4 C7 C4 173.4(2) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1 0 1 0.1580 -1.0005 -0.0003 0.9997 -0.1132 -0.0550 -0.0020
1 0 -1 0.1580 1.0005 0.0003 -0.9997 0.1132 0.0550 0.0020
0 -1 0 0.0985 -0.0008 -0.9990 0.0010 -0.0046 -0.0026 0.1117
0 1 0 0.0985 0.0008 0.9990 -0.0010 0.0046 0.0026 -0.1117
0 0 1 0.0242 -0.0003 -0.0001 1.0009 -0.0290 0.0348 -0.0095
0 0 -1 0.0242 0.0003 0.0001 -1.0009 0.0290 -0.0348 0.0095

_iucr_refinement_instructions_details 
;
TITL 15srv065 in P-1 #2
REM reset to P-1 #2
CELL 0.71073 5.820976 6.487541 15.748505 100.7378 96.6255 94.6122
ZERR 2 0.000371 0.00051 0.001216 0.0067 0.0058 0.0059
LATT 1
SFAC C H Cl F N O
UNIT 16 30 2 2 2 8
EQIV $1 -1+X,+Y,+Z
EQIV $2 1-X,2-Y,1-Z

L.S. 9
PLAN  5
TEMP -153.15
HTAB N1 Cl1_$1
HTAB N1 Cl1
HTAB N1 Cl1_$2
BOND $h
CONF 
fmap 2 53
ACTA 
OMIT -2 56
OMIT 0 -1 6
OMIT -3 -2 4
WGHT 0.035 0.8
FVAR 8.08591
REM <olex2.extras>
REM <HklSrc "%.\\15srv065.hkl">
REM </olex2.extras>

Cl1   3     0.75418  1.29673  0.51960  11.00000  0.01597  0.01425  0.03024 =
 0.00499  0.00285  0.00124 
F1    4     0.68307  0.98869  0.17917  11.00000  0.02105  0.02103  0.03176 =
 0.00861  0.00146 -0.00638 
O1    6     0.55946  0.76911  0.01629  11.00000  0.02949  0.04837  0.02880 =
 0.00558  0.00774  0.00710 
O2    6     0.18710  0.76201  0.04072  11.00000  0.02275  0.03191  0.02152 =
 0.00814  0.00003 -0.00378 
O3    6     0.35966  0.52046  0.19529  11.00000  0.03137  0.01605  0.03308 =
 0.00794 -0.00201 -0.00380 
O4    6     0.71770  0.68003  0.24970  11.00000  0.02896  0.01721  0.03721 =
 0.00708 -0.00891  0.00370 
N1    5     0.22167  1.17720  0.44695  11.00000  0.01717  0.01385  0.02716 =
 0.00203  0.00427  0.00290 
AFIX 137
H1a   2     0.22289  1.04776  0.46134  11.00000 -1.20000 
H1b   2     0.10864  1.24605  0.47189  11.00000 -1.20000 
H1c   2     0.36231  1.25303  0.46662  11.00000 -1.20000 
AFIX 0
C1    1     0.17450  1.15230  0.35047  11.00000  0.02185  0.01918  0.02627 =
 0.00251  0.00038  0.00595 
AFIX 23
H1d   2     0.18309  1.29298  0.33448  11.00000 -1.20000 
H1e   2     0.01570  1.08124  0.32955  11.00000 -1.20000 
AFIX 0
C2    1     0.35012  1.02328  0.30724  11.00000  0.02138  0.01667  0.02291 =
 0.00381  0.00165  0.00527 
AFIX 23
H2a   2     0.35185  0.88815  0.32781  11.00000 -1.20000 
H2b   2     0.50720  1.10086  0.32416  11.00000 -1.20000 
AFIX 0
C3    1     0.29164  0.97854  0.20797  11.00000  0.02291  0.01590  0.02321 =
 0.00485  0.00066  0.00470 
AFIX 23
H3a   2     0.13797  0.89465  0.19101  11.00000 -1.20000 
H3b   2     0.28147  1.11363  0.18781  11.00000 -1.20000 
AFIX 0
C4    1     0.47370  0.85891  0.16362  11.00000  0.01650  0.01395  0.02553 =
 0.00640  0.00054 -0.00270 
C5    1     0.41507  0.79095  0.06354  11.00000  0.02593  0.01585  0.02350 =
 0.00661  0.00223  0.00158 
C6    1     0.10737  0.69482 -0.05202  11.00000  0.03485  0.03693  0.02158 =
 0.00821 -0.00371 -0.00750 
AFIX 137
H6a   2     0.17218  0.79776 -0.08352  11.00000 -1.50000 
H6b   2    -0.06283  0.68484 -0.06201  11.00000 -1.50000 
H6c   2     0.15899  0.55656 -0.07308  11.00000 -1.50000 
AFIX 0
C7    1     0.51043  0.66310  0.20300  11.00000  0.02211  0.01618  0.02026 =
 0.00258  0.00232  0.00347 
C8    1     0.75462  0.51060  0.29698  11.00000  0.05491  0.02148  0.05272 =
 0.01206 -0.02718  0.00688 
AFIX 137
H8a   2     0.74655  0.37666  0.25540  11.00000 -1.50000 
H8b   2     0.63416  0.50186  0.33518  11.00000 -1.50000 
H8c   2     0.90801  0.53912  0.33222  11.00000 -1.50000 
AFIX 0
HKLF 4

END
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4d_14srv042
_database_code_depnum_ccdc_archive 'CCDC 1401920'
_audit_update_record             
;
2015-05-20 deposited with the CCDC.
2015-10-13 downloaded from the CCDC.
;
_audit_creation_date             2014-02-20
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.02.17 svn.r2891 for OlexSys, GUI svn.r4773)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
(rac)-methyl 3-fluoro-2-oxopiperidine-3-carboxylate 
;
_chemical_formula_moiety         'C7 H10 F N O3'
_chemical_formula_sum            'C7 H10 F N O3'
_chemical_formula_weight         175.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C7 H10 F1 N1 O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   12.2560(4)
_cell_length_b                   6.72544(17)
_cell_length_c                   10.4787(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.193(4)
_cell_angle_gamma                90.00
_cell_volume                     793.93(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4749
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      32.5790
_cell_measurement_theta_min      1.8150
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94438
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14038
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         3.53
_diffrn_ambient_temperature      120.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Agilent Xcalibur'
_diffrn_measurement_method       ω-scan
_diffrn_orient_matrix_UB_11      0.0098259000
_diffrn_orient_matrix_UB_12      -0.0947619000
_diffrn_orient_matrix_UB_13      -0.0232601000
_diffrn_orient_matrix_UB_21      0.0160497000
_diffrn_orient_matrix_UB_22      0.0462023000
_diffrn_orient_matrix_UB_23      -0.0509704000
_diffrn_orient_matrix_UB_31      0.0600403000
_diffrn_orient_matrix_UB_32      0.0031482000
_diffrn_orient_matrix_UB_33      0.0478793000
_diffrn_radiation_collimation    monochromator
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2020
_reflns_number_total             2324
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.93
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2324
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0500P)²+0.1900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0942
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
F1 F 0.77798(6) 1.00559(10) 0.72182(6) 0.02313(16) Uani 1 d . . .
O1 O 0.88589(7) 1.12138(10) 0.53344(8) 0.02062(17) Uani 1 d . . .
O2 O 0.62666(6) 0.97186(10) 0.35850(7) 0.01704(16) Uani 1 d . . .
O3 O 0.60288(7) 1.18044(12) 0.51438(8) 0.02513(19) Uani 1 d . . .
N1 N 0.93017(7) 0.79229(12) 0.56406(9) 0.01582(17) Uani 1 d . . .
C1 C 0.86321(8) 0.94999(14) 0.55960(10) 0.01408(18) Uani 1 d . . .
C2 C 0.75183(8) 0.91935(14) 0.59126(9) 0.01446(18) Uani 1 d . . .
C3 C 0.71776(9) 0.70253(15) 0.59688(11) 0.0192(2) Uani 1 d . . .
C4 C 0.82841(9) 0.57784(16) 0.67313(11) 0.0189(2) Uani 1 d . . .
C5 C 0.90752(9) 0.58519(14) 0.59288(11) 0.0174(2) Uani 1 d . . .
C6 C 0.65139(8) 1.04246(14) 0.48597(10) 0.01509(19) Uani 1 d . . .
C7 C 0.53792(10) 1.08278(18) 0.24668(11) 0.0235(2) Uani 1 d . . .
H1 H 0.9892(14) 0.818(2) 0.5387(15) 0.028(4) Uiso 1 d . . .
H3A H 0.6781(13) 0.651(2) 0.5013(15) 0.023(3) Uiso 1 d . . .
H3B H 0.6619(14) 0.699(2) 0.6431(16) 0.031(4) Uiso 1 d . . .
H4A H 0.8094(13) 0.442(2) 0.6855(15) 0.025(3) Uiso 1 d . . .
H4B H 0.8707(13) 0.630(2) 0.7655(16) 0.027(4) Uiso 1 d . . .
H5A H 0.8708(13) 0.515(2) 0.5032(15) 0.023(3) Uiso 1 d . . .
H5B H 0.9843(14) 0.524(2) 0.6432(16) 0.026(4) Uiso 1 d . . .
H7A H 0.4688(14) 1.107(2) 0.2659(15) 0.030(4) Uiso 1 d . . .
H7B H 0.5707(15) 1.205(3) 0.2357(17) 0.037(4) Uiso 1 d . . .
H7C H 0.5167(15) 0.999(2) 0.1637(17) 0.033(4) Uiso 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.4020(11) . ?
O1 C1 1.2414(12) . ?
O2 C6 1.3352(12) . ?
O2 C7 1.4521(12) . ?
O3 C6 1.2011(12) . ?
N1 C1 1.3305(12) . ?
N1 C5 1.4746(12) . ?
N1 H1 0.881(16) . ?
C1 C2 1.5403(13) . ?
C2 C3 1.5243(13) . ?
C2 C6 1.5325(13) . ?
C3 C4 1.5255(14) . ?
C3 H3A 0.987(14) . ?
C3 H3B 0.983(15) . ?
C4 C5 1.5139(15) . ?
C4 H4A 0.964(15) . ?
C4 H4B 0.966(15) . ?
C5 H5A 0.987(14) . ?
C5 H5B 0.972(15) . ?
C7 H7A 0.959(16) . ?
C7 H7B 0.939(17) . ?
C7 H7C 0.980(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O2 C7 115.30(8) . . ?
C1 N1 C5 126.65(8) . . ?
C1 N1 H1 113.7(10) . . ?
C5 N1 H1 119.3(10) . . ?
O1 C1 N1 124.00(9) . . ?
O1 C1 C2 117.79(8) . . ?
N1 C1 C2 118.19(8) . . ?
F1 C2 C1 105.87(7) . . ?
F1 C2 C3 108.60(8) . . ?
F1 C2 C6 106.80(8) . . ?
C3 C2 C1 114.57(8) . . ?
C3 C2 C6 112.96(8) . . ?
C6 C2 C1 107.54(8) . . ?
C2 C3 C4 110.22(8) . . ?
C2 C3 H3A 109.2(8) . . ?
C2 C3 H3B 107.3(9) . . ?
C4 C3 H3A 108.7(8) . . ?
C4 C3 H3B 112.1(9) . . ?
H3A C3 H3B 109.3(12) . . ?
C3 C4 H4A 112.3(9) . . ?
C3 C4 H4B 109.9(9) . . ?
C5 C4 C3 108.83(8) . . ?
C5 C4 H4A 110.3(9) . . ?
C5 C4 H4B 109.7(9) . . ?
H4A C4 H4B 105.8(12) . . ?
N1 C5 C4 110.97(8) . . ?
N1 C5 H5A 107.9(8) . . ?
N1 C5 H5B 107.1(9) . . ?
C4 C5 H5A 111.2(9) . . ?
C4 C5 H5B 112.3(9) . . ?
H5A C5 H5B 107.2(12) . . ?
O2 C6 C2 109.25(8) . . ?
O3 C6 O2 125.68(9) . . ?
O3 C6 C2 125.08(9) . . ?
O2 C7 H7A 111.2(9) . . ?
O2 C7 H7B 109.1(10) . . ?
O2 C7 H7C 105.9(10) . . ?
H7A C7 H7B 109.3(14) . . ?
H7A C7 H7C 109.7(14) . . ?
H7B C7 H7C 111.6(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.881(16) 1.998(16) 2.8770(11) 175.7(14) 3_776

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C2 C3 C4 -76.45(10) . . . . ?
F1 C2 C6 O2 177.17(7) . . . . ?
F1 C2 C6 O3 -2.89(13) . . . . ?
O1 C1 C2 F1 -70.70(11) . . . . ?
O1 C1 C2 C3 169.66(9) . . . . ?
O1 C1 C2 C6 43.19(11) . . . . ?
N1 C1 C2 F1 108.25(9) . . . . ?
N1 C1 C2 C3 -11.39(12) . . . . ?
N1 C1 C2 C6 -137.85(9) . . . . ?
C1 N1 C5 C4 -23.07(14) . . . . ?
C1 C2 C3 C4 41.65(11) . . . . ?
C1 C2 C6 O2 63.90(10) . . . . ?
C1 C2 C6 O3 -116.16(11) . . . . ?
C2 C3 C4 C5 -62.56(11) . . . . ?
C3 C2 C6 O2 -63.50(10) . . . . ?
C3 C2 C6 O3 116.43(11) . . . . ?
C3 C4 C5 N1 52.18(11) . . . . ?
C5 N1 C1 O1 -179.27(9) . . . . ?
C5 N1 C1 C2 1.85(14) . . . . ?
C6 C2 C3 C4 165.27(8) . . . . ?
C7 O2 C6 O3 3.87(15) . . . . ?
C7 O2 C6 C2 -176.19(8) . . . . ?

_iucr_refinement_instructions_details 
;
TITL 14srv042 in P2(1)/c
CELL 0.71073 12.255998 6.725436 10.478718 90 113.1927 90
ZERR 4 0.000433 0.000169 0.000368 0 0.0041 0
LATT 1
SYMM -X,0.5+Y,0.5-Z

SFAC C H N O F
UNIT 28 40 4 12 4
EQIV $1 2-X,2-Y,1-Z


L.S. 9
PLAN  5
HTAB N1 O1_$1
CONF 
BOND $h
fmap 2
acta 
OMIT -2 60
OMIT 1 0 0
REM <HKL>T:/People/DSY/14srv042/struct/14srv042.hkl</HKL>
WGHT 0.05 0.19
FVAR 8.88068

F1    5     0.77798  1.00559  0.72182  11.00000  0.02443  0.03123  0.01408 =
 -0.00505  0.00792  0.00093 
O1    4     0.88589  1.12137  0.53343  11.00000  0.02054  0.01246  0.03277 =
 0.00061  0.01467 -0.00157 
O2    4     0.62666  0.97186  0.35850  11.00000  0.01870  0.01689  0.01452 =
 0.00109  0.00543  0.00554 
O3    4     0.60288  1.18044  0.51438  11.00000  0.02688  0.02454  0.02494 =
 -0.00363  0.01122  0.00871 
N1    3     0.93017  0.79230  0.56406  11.00000  0.01489  0.01324  0.02133 =
 0.00110  0.00925 -0.00030 
C1    1     0.86321  0.94998  0.55960  11.00000  0.01318  0.01457  0.01408 =
 -0.00143  0.00490 -0.00223 
C2    1     0.75184  0.91934  0.59126  11.00000  0.01460  0.01633  0.01321 =
 -0.00073  0.00625 -0.00108 
C3    1     0.71776  0.70253  0.59688  11.00000  0.01623  0.01805  0.02440 =
 0.00561  0.00914 -0.00151 
C4    1     0.82841  0.57785  0.67313  11.00000  0.02010  0.01809  0.01861 =
 0.00598  0.00773  0.00040 
C5    1     0.90752  0.58518  0.59288  11.00000  0.01895  0.01288  0.02066 =
 0.00294  0.00817  0.00090 
C6    1     0.65139  1.04246  0.48598  11.00000  0.01480  0.01465  0.01751 =
 -0.00005  0.00813 -0.00075 
C7    1     0.53792  1.08279  0.24668  11.00000  0.02571  0.02554  0.01805 =
 0.00605  0.00738  0.01150 
H1    2     0.98924  0.81789  0.53869  11.00000  0.02814 
H3a   2     0.67816  0.65124  0.50136  11.00000  0.02289 
H3b   2     0.66183  0.69899  0.64308  11.00000  0.03075 
H4a   2     0.80933  0.44211  0.68543  11.00000  0.02541 
H4b   2     0.87065  0.62998  0.76549  11.00000  0.02719 
H5a   2     0.87075  0.51537  0.50319  11.00000  0.02312 
H5b   2     0.98429  0.52357  0.64327  11.00000  0.02603 
H7a   2     0.46883  1.10732  0.26593  11.00000  0.03022 
H7b   2     0.57077  1.20460  0.23569  11.00000  0.03716 
H7c   2     0.51676  0.99916  0.16377  11.00000  0.03353 
HKLF 4
END
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_8_14srv004
_database_code_depnum_ccdc_archive 'CCDC 1401921'
_audit_update_record             
;
2015-05-20 deposited with the CCDC.
2015-10-13 downloaded from the CCDC.
;
_audit_creation_date             2014-04-04
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'Cl, C7 H13 F N O4'
_chemical_formula_sum            'C7 H13 Cl F N O4'
_chemical_formula_weight         229.63
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   12.2350(7)
_cell_length_b                   11.3068(7)
_cell_length_c                   7.6415(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.2891(17)
_cell_angle_gamma                90.00
_cell_volume                     1040.12(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9971
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.54
_cell_measurement_theta_min      2.47
_exptl_absorpt_coefficient_mu    0.372
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0920 before and 0.0733 after correction.
The Ratio of minimum to maximum transmission is 0.9261.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            21745
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.47
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  D8Venture
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'ImuS microsource'
_diffrn_special_details          ?
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                2721
_reflns_number_total             3038
_reflns_threshold_expression     >2sigma(I)
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         3038
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0341
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0500P)²+0.1700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0873
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.501476(19) 0.85721(2) 0.20873(3) 0.01750(9) Uani 1 d . . .
F1 F 0.82834(5) 0.67909(5) 0.01818(8) 0.01878(14) Uani 1 d . . .
O1 O 0.87659(6) 0.39998(7) 0.21097(11) 0.02117(17) Uani 1 d . . .
O2 O 0.99028(7) 0.55145(7) 0.18471(12) 0.02671(19) Uani 1 d . . .
O3 O 0.75641(6) 0.39687(7) -0.15572(9) 0.01785(16) Uani 1 d . . .
O4 O 0.77481(6) 0.57242(7) -0.28658(10) 0.01928(16) Uani 1 d . . .
N1 N 0.60238(9) 0.61344(9) 0.35824(13) 0.02004(19) Uani 1 d . . .
C1 C 0.80051(8) 0.56142(8) 0.03289(12) 0.01301(18) Uani 1 d . . .
C2 C 0.69467(8) 0.55431(9) 0.11183(12) 0.01387(18) Uani 1 d . . .
C3 C 0.71079(9) 0.60942(10) 0.29601(13) 0.0188(2) Uani 1 d . . .
C4 C 0.90168(8) 0.50422(9) 0.15045(12) 0.01393(18) Uani 1 d . . .
C5 C 0.96777(10) 0.33852(11) 0.32313(18) 0.0257(2) Uani 1 d . . .
C6 C 0.77742(8) 0.51151(9) -0.15736(13) 0.01372(18) Uani 1 d . . .
C7 C 0.72684(11) 0.34234(11) -0.32981(16) 0.0251(2) Uani 1 d . . .
H1A H 0.6123(13) 0.6254(14) 0.477(2) 0.030(4) Uiso 1 d . . .
H1B H 0.5657(13) 0.5449(14) 0.333(2) 0.026(4) Uiso 1 d . . .
H1C H 0.5637(14) 0.6708(15) 0.309(2) 0.032(4) Uiso 1 d . . .
H2A H 0.6726(11) 0.4728(12) 0.1148(17) 0.016(3) Uiso 1 d . . .
H2B H 0.6366(11) 0.5959(13) 0.0339(18) 0.017(3) Uiso 1 d . . .
H3A H 0.7387(12) 0.6874(14) 0.2945(19) 0.024(4) Uiso 1 d . . .
H3B H 0.7635(12) 0.5633(13) 0.3807(19) 0.021(3) Uiso 1 d . . .
H5A H 0.9390(13) 0.2630(15) 0.351(2) 0.032(4) Uiso 1 d . . .
H5B H 0.9948(16) 0.3867(17) 0.427(2) 0.047(5) Uiso 1 d . . .
H5C H 1.0238(17) 0.3250(18) 0.263(3) 0.048(5) Uiso 1 d . . .
H7A H 0.6624(14) 0.3808(14) -0.397(2) 0.030(4) Uiso 1 d . . .
H7B H 0.7068(14) 0.2623(15) -0.308(2) 0.033(4) Uiso 1 d . . .
H7C H 0.7868(15) 0.3470(14) -0.390(2) 0.032(4) Uiso 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.3829(11) . ?
O1 C4 1.3222(12) . ?
O1 C5 1.4562(13) . ?
O2 C4 1.1948(12) . ?
O3 C6 1.3219(12) . ?
O3 C7 1.4522(13) . ?
O4 C6 1.1996(12) . ?
N1 C3 1.4877(14) . ?
N1 H1A 0.907(17) . ?
N1 H1B 0.899(16) . ?
N1 H1C 0.850(18) . ?
C1 C2 1.5252(13) . ?
C1 C4 1.5362(13) . ?
C1 C6 1.5379(13) . ?
C2 C3 1.5194(13) . ?
C2 H2A 0.961(14) . ?
C2 H2B 0.964(14) . ?
C3 H3A 0.946(16) . ?
C3 H3B 0.979(15) . ?
C5 H5A 0.963(16) . ?
C5 H5B 0.972(19) . ?
C5 H5C 0.91(2) . ?
C7 H7A 0.963(17) . ?
C7 H7B 0.961(17) . ?
C7 H7C 0.935(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 C5 115.46(8) . . ?
C6 O3 C7 115.13(8) . . ?
C3 N1 H1A 111.0(10) . . ?
C3 N1 H1B 110.3(10) . . ?
C3 N1 H1C 109.8(11) . . ?
H1A N1 H1B 108.2(14) . . ?
H1A N1 H1C 107.3(15) . . ?
H1B N1 H1C 110.2(14) . . ?
F1 C1 C2 108.76(8) . . ?
F1 C1 C4 105.56(7) . . ?
F1 C1 C6 106.41(7) . . ?
C2 C1 C4 113.51(8) . . ?
C2 C1 C6 109.20(7) . . ?
C4 C1 C6 113.02(8) . . ?
C1 C2 H2A 108.7(8) . . ?
C1 C2 H2B 108.3(8) . . ?
C3 C2 C1 111.46(8) . . ?
C3 C2 H2A 111.2(8) . . ?
C3 C2 H2B 109.4(8) . . ?
H2A C2 H2B 107.6(11) . . ?
N1 C3 C2 109.45(9) . . ?
N1 C3 H3A 108.6(9) . . ?
N1 C3 H3B 109.0(9) . . ?
C2 C3 H3A 111.0(9) . . ?
C2 C3 H3B 110.8(8) . . ?
H3A C3 H3B 107.9(12) . . ?
O1 C4 C1 111.51(8) . . ?
O2 C4 O1 125.46(9) . . ?
O2 C4 C1 123.01(9) . . ?
O1 C5 H5A 106.4(10) . . ?
O1 C5 H5B 109.1(11) . . ?
O1 C5 H5C 110.5(12) . . ?
H5A C5 H5B 113.6(14) . . ?
H5A C5 H5C 107.7(16) . . ?
H5B C5 H5C 109.5(17) . . ?
O3 C6 C1 110.73(8) . . ?
O4 C6 O3 126.45(9) . . ?
O4 C6 C1 122.74(9) . . ?
O3 C7 H7A 109.9(10) . . ?
O3 C7 H7B 105.5(10) . . ?
O3 C7 H7C 109.8(10) . . ?
H7A C7 H7B 108.0(14) . . ?
H7A C7 H7C 110.6(14) . . ?
H7B C7 H7C 112.8(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A Cl1 0.907(17) 2.421(17) 3.1605(9) 138.9(13) 4_576
N1 H1A O4 0.907(17) 2.506(16) 3.1602(13) 129.3(13) 1_556
N1 H1B Cl1 0.899(16) 2.278(16) 3.1682(10) 170.8(13) 2_645
N1 H1C Cl1 0.850(18) 2.324(18) 3.1499(10) 164.0(15) .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 C3 -60.80(10) . . . . ?
F1 C1 C4 O1 164.51(8) . . . . ?
F1 C1 C4 O2 -13.61(13) . . . . ?
F1 C1 C6 O3 176.27(7) . . . . ?
F1 C1 C6 O4 -6.73(12) . . . . ?
C1 C2 C3 N1 173.26(8) . . . . ?
C2 C1 C4 O1 45.49(11) . . . . ?
C2 C1 C4 O2 -132.63(10) . . . . ?
C2 C1 C6 O3 -66.50(10) . . . . ?
C2 C1 C6 O4 110.50(10) . . . . ?
C4 C1 C2 C3 56.37(11) . . . . ?
C4 C1 C6 O3 60.87(10) . . . . ?
C4 C1 C6 O4 -122.13(10) . . . . ?
C5 O1 C4 O2 -2.31(16) . . . . ?
C5 O1 C4 C1 179.63(9) . . . . ?
C6 C1 C2 C3 -176.53(8) . . . . ?
C6 C1 C4 O1 -79.59(10) . . . . ?
C6 C1 C4 O2 102.30(11) . . . . ?
C7 O3 C6 O4 -0.41(14) . . . . ?
C7 O3 C6 C1 176.45(9) . . . . ?

_iucr_refinement_instructions_details 
;
TITL 14srv004 in P21/c #14
CELL 0.71073 12.235 11.3068 7.6415 90 100.2891 90
ZERR 4 0.0007 0.0007 0.0004 0 0.0017 0
LATT 1
SYMM -X,0.5+Y,0.5-Z

SFAC C H N O F Cl
UNIT 28 52 4 16 4 4
EQIV $1 1-X,-0.5+Y,0.5-Z
EQIV $2 +X,1.5-Y,0.5+Z
EQIV $3 +X,+Y,1+Z


L.S. 9
PLAN  5
HTAB N1 Cl1
HTAB N1 Cl1_$1
HTAB N1 Cl1_$2
HTAB N1 O4_$3
CONF 
REM reset to P21/c #14
BOND $h
fmap 2 53
acta 
OMIT -2 60
OMIT 0 2 1
REM <HKL>D:/Struc/14S/14srv104/14srv004.hkl</HKL>
WGHT 0.05 0.17
FVAR 0.21237

Cl1   6     0.50148  0.85721  0.20873  11.00000  0.01823  0.01942  0.01470 =
 0.00247  0.00256  0.00198 

F1    5     0.82834  0.67909  0.01818  11.00000  0.02332  0.01136  0.02036 =
 0.00334  0.00034 -0.00274 
O1    4     0.87658  0.39998  0.21097  11.00000  0.01598  0.01675  0.02801 =
 0.00930 -0.00360 -0.00089 
O2    4     0.99028  0.55145  0.18471  11.00000  0.01592  0.02081  0.04005 =
 0.00611 -0.00406 -0.00379 
O3    4     0.75641  0.39687 -0.15572  11.00000  0.02231  0.01657  0.01382 =
 -0.00249  0.00093 -0.00113 
O4    4     0.77480  0.57242 -0.28658  11.00000  0.01933  0.02442  0.01401 =
 0.00450  0.00276  0.00167 
N1    3     0.60237  0.61344  0.35824  11.00000  0.02907  0.01585  0.01721 =
 -0.00016  0.00963  0.00307 
C1    1     0.80051  0.56142  0.03289  11.00000  0.01496  0.01055  0.01279 =
 0.00147  0.00051 -0.00096 
C2    1     0.69467  0.55431  0.11183  11.00000  0.01536  0.01513  0.01075 =
 -0.00064  0.00134  0.00087 
C3    1     0.71079  0.60942  0.29601  11.00000  0.02230  0.02044  0.01321 =
 -0.00328  0.00221 -0.00047 
C4    1     0.90168  0.50422  0.15045  11.00000  0.01499  0.01357  0.01286 =
 0.00002  0.00148  0.00049 
C5    1     0.96777  0.33852  0.32314  11.00000  0.02145  0.02010  0.03187 =
 0.00965 -0.00549  0.00375 
C6    1     0.77742  0.51151 -0.15736  11.00000  0.01047  0.01704  0.01349 =
 0.00006  0.00175  0.00133 
C7    1     0.72684  0.34234 -0.32981  11.00000  0.03015  0.02566  0.01774 =
 -0.00770 -0.00054 -0.00006 
H1a   2     0.61233  0.62537  0.47741  11.00000  0.03004 
H1b   2     0.56567  0.54493  0.33336  11.00000  0.02574 
H1c   2     0.56369  0.67079  0.30879  11.00000  0.03205 
H2a   2     0.67264  0.47283  0.11480  11.00000  0.01580 
H2b   2     0.63659  0.59585  0.03394  11.00000  0.01697 
H3a   2     0.73868  0.68737  0.29454  11.00000  0.02401 
H3b   2     0.76352  0.56330  0.38070  11.00000  0.02117 
H5a   2     0.93904  0.26296  0.35119  11.00000  0.03204 
H5b   2     0.99483  0.38669  0.42715  11.00000  0.04677 
H5c   2     1.02384  0.32503  0.26257  11.00000  0.04771 
H7a   2     0.66239  0.38078 -0.39672  11.00000  0.02983 
H7b   2     0.70681  0.26227 -0.30760  11.00000  0.03272 
H7c   2     0.78675  0.34701 -0.39017  11.00000  0.03237 
HKLF 4
END
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_9_14srv109
_database_code_depnum_ccdc_archive 'CCDC 1401922'
_audit_update_record             
;
2015-05-20 deposited with the CCDC.
2015-10-13 downloaded from the CCDC.
;
_audit_creation_date             2014-04-11
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 methyl 3-fluoro-2-oxo-3-pyrrolidinecarboxylate
;
_chemical_formula_moiety         'C6 H8 F N O3, H2 O'
_chemical_formula_sum            'C6 H10 F N O4'
_chemical_formula_weight         179.15
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   6.5648(7)
_cell_length_b                   6.6759(7)
_cell_length_c                   9.6206(10)
_cell_angle_alpha                98.163(3)
_cell_angle_beta                 100.929(3)
_cell_angle_gamma                101.047(3)
_cell_volume                     399.30(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3503
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.57
_cell_measurement_theta_min      3.16
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1445 before and 0.0996 after correction.
The Ratio of minimum to maximum transmission is 0.6623.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'dull light colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             188
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_av_unetI/netI     0.0681
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6012
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         3.16
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  D8Venture
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'ImuS microsource'
_diffrn_special_details          ?
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                1877
_reflns_number_total             2317
_reflns_threshold_expression     >2sigma(I)
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0548
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0900P)²+0.0400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1501
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
F1 F 0.38979(12) 0.50223(13) 0.16612(9) 0.0208(2) Uani 1 d . . .
O1 O 0.66817(16) 0.85861(15) 0.12521(11) 0.0210(3) Uani 1 d . . .
O2 O 0.43275(16) 0.69399(15) 0.43221(11) 0.0209(3) Uani 1 d . . .
O3 O 0.79024(15) 0.75684(15) 0.46786(10) 0.0185(2) Uani 1 d . . .
N1 N 0.90694(19) 0.64960(18) 0.16237(13) 0.0167(3) Uani 1 d . . .
C1 C 0.7281(2) 0.7094(2) 0.16881(14) 0.0151(3) Uani 1 d . . .
C2 C 0.5981(2) 0.5627(2) 0.24550(14) 0.0150(3) Uani 1 d . . .
C3 C 0.7081(2) 0.3817(2) 0.24868(16) 0.0180(3) Uani 1 d . . .
C4 C 0.9326(2) 0.4703(2) 0.22986(16) 0.0184(3) Uani 1 d . . .
C5 C 0.5925(2) 0.67779(19) 0.39273(14) 0.0146(3) Uani 1 d . . .
C6 C 0.8084(3) 0.8764(2) 0.60989(16) 0.0210(3) Uani 1 d . . .
H1 H 1.007(3) 0.719(3) 0.132(2) 0.028(5) Uiso 1 d . . .
H3A H 0.707(3) 0.330(3) 0.335(2) 0.036(5) Uiso 1 d . . .
H3B H 0.628(3) 0.276(3) 0.167(2) 0.026(5) Uiso 1 d . . .
H4A H 1.038(3) 0.510(3) 0.324(2) 0.023(4) Uiso 1 d . . .
H4B H 0.987(3) 0.369(3) 0.169(2) 0.028(5) Uiso 1 d . . .
H6A H 0.750(4) 0.793(3) 0.668(2) 0.036(5) Uiso 1 d . . .
H6B H 0.960(3) 0.921(3) 0.646(2) 0.023(4) Uiso 1 d . . .
H6C H 0.744(3) 0.994(3) 0.600(2) 0.026(5) Uiso 1 d . . .
O4 O 0.23967(17) 0.91176(17) 0.08602(13) 0.0218(3) Uani 1 d . . .
H4C H 0.362(4) 0.882(3) 0.102(3) 0.040(6) Uiso 1 d . . .
H4D H 0.239(4) 0.981(3) 0.020(3) 0.041(6) Uiso 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.3858(15) . ?
O1 C1 1.2369(16) . ?
O2 C5 1.1995(16) . ?
O3 C5 1.3264(16) . ?
O3 C6 1.4528(17) . ?
N1 C1 1.3196(17) . ?
N1 C4 1.4626(18) . ?
N1 H1 0.85(2) . ?
C1 C2 1.5348(19) . ?
C2 C3 1.5230(18) . ?
C2 C5 1.5228(18) . ?
C3 C4 1.534(2) . ?
C3 H3A 0.95(2) . ?
C3 H3B 0.966(19) . ?
C4 H4A 0.993(19) . ?
C4 H4B 0.994(19) . ?
C6 H6A 0.92(2) . ?
C6 H6B 0.962(19) . ?
C6 H6C 0.967(19) . ?
O4 H4C 0.86(2) . ?
O4 H4D 0.84(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O3 C6 115.04(11) . . ?
C1 N1 C4 114.51(12) . . ?
C1 N1 H1 122.9(13) . . ?
C4 N1 H1 122.1(13) . . ?
O1 C1 N1 128.40(13) . . ?
O1 C1 C2 123.06(12) . . ?
N1 C1 C2 108.53(11) . . ?
F1 C2 C1 108.65(10) . . ?
F1 C2 C3 112.29(10) . . ?
F1 C2 C5 107.01(10) . . ?
C3 C2 C1 103.90(10) . . ?
C5 C2 C1 109.85(10) . . ?
C5 C2 C3 115.00(11) . . ?
C2 C3 C4 104.54(11) . . ?
C2 C3 H3A 110.7(12) . . ?
C2 C3 H3B 106.0(11) . . ?
C4 C3 H3A 113.5(13) . . ?
C4 C3 H3B 111.4(11) . . ?
H3A C3 H3B 110.3(16) . . ?
N1 C4 C3 103.39(11) . . ?
N1 C4 H4A 112.4(11) . . ?
N1 C4 H4B 111.3(11) . . ?
C3 C4 H4A 111.6(11) . . ?
C3 C4 H4B 112.8(11) . . ?
H4A C4 H4B 105.6(15) . . ?
O2 C5 O3 126.21(12) . . ?
O2 C5 C2 124.53(12) . . ?
O3 C5 C2 109.25(11) . . ?
O3 C6 H6A 110.7(12) . . ?
O3 C6 H6B 102.9(11) . . ?
O3 C6 H6C 109.4(11) . . ?
H6A C6 H6B 109.6(17) . . ?
H6A C6 H6C 112.6(17) . . ?
H6B C6 H6C 111.3(15) . . ?
H4C O4 H4D 106(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O4 0.85(2) 1.96(2) 2.8076(16) 171.8(17) 1_655
O4 H4C O1 0.86(2) 2.02(2) 2.8635(15) 170(2) .
O4 H4D O1 0.84(3) 1.99(3) 2.8002(15) 162(2) 2_675

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 F1 48.39(16) . . . . ?
O2 C5 C2 F1 5.66(17) . . . . ?
O3 C5 C2 F1 -173.84(9) . . . . ?
N1 C1 C2 F1 -132.86(11) . . . . ?
C1 C2 C3 C4 21.19(13) . . . . ?
C1 C2 C5 O2 123.44(13) . . . . ?
C1 C2 C5 O3 -56.07(13) . . . . ?
C2 C1 N1 C4 -1.14(15) . . . . ?
C2 C3 C4 N1 -21.72(14) . . . . ?
C3 C2 C1 O1 168.12(12) . . . . ?
C3 C2 C1 N1 -13.13(14) . . . . ?
C3 C2 C5 O2 -119.81(14) . . . . ?
C3 C2 C5 O3 60.68(14) . . . . ?
C3 C4 N1 C1 14.78(15) . . . . ?
C4 N1 C1 O1 177.53(13) . . . . ?
C4 C3 C2 F1 138.42(11) . . . . ?
C4 C3 C2 C5 -98.90(13) . . . . ?
C5 C2 C1 O1 -68.36(15) . . . . ?
C5 C2 C1 N1 110.39(12) . . . . ?

_iucr_refinement_instructions_details 
;
TITL 14srv109 in P-1 #2
CELL 0.71073 6.5648 6.6759 9.6206 98.1632 100.9289 101.0472
ZERR 2 0.0007 0.0007 0.001 0.0034 0.0033 0.0034
LATT 1

SFAC C H F N O
UNIT 12 20 2 2 8
EQIV $1 1-X,2-Y,-Z
EQIV $2 1+X,+Y,+Z


L.S. 9
PLAN  5
TEMP -153.15
HTAB O4 O1
HTAB O4 O1_$1
HTAB N1 O4_$2
CONF C4 N1 C1 O1
CONF C2 C1 N1 C4
CONF O1 C1 C2 F1
CONF N1 C1 C2 F1
CONF C3 C2 C1 O1
CONF C3 C2 C1 N1
CONF C5 C2 C1 O1
CONF C5 C2 C1 N1
CONF C4 C3 C2 F1
CONF C1 C2 C3 C4
CONF C4 C3 C2 C5
CONF C2 C3 C4 N1
CONF C3 C4 N1 C1
CONF O2 C5 C2 F1
CONF C1 C2 C5 O2
CONF C3 C2 C5 O2
CONF O3 C5 C2 F1
CONF C1 C2 C5 O3
CONF C3 C2 C5 O3
REM reset to P-1 #2
BOND $h
fmap 2 53
acta 
OMIT -2 60
OMIT 0 0 1
OMIT 0 -2 2
REM <HKL>D:/Struc/14S/14srv109/14srv109.hkl</HKL>
WGHT 0.09 0.04
FVAR 0.42513

F1    3     0.38979  0.50223  0.16612  11.00000  0.01303  0.02709  0.01845 =
 0.00111  0.00067  0.00021 
O1    5     0.66817  0.85861  0.12521  11.00000  0.02366  0.02265  0.02137 =
 0.01055  0.00733  0.00943 
O2    5     0.43275  0.69399  0.43221  11.00000  0.01805  0.02584  0.02134 =
 0.00364  0.00771  0.00826 
O3    5     0.79024  0.75684  0.46786  11.00000  0.01708  0.02122  0.01514 =
 -0.00092  0.00288  0.00306 
N1    4     0.90694  0.64960  0.16237  11.00000  0.01465  0.02002  0.01676 =
 0.00511  0.00598  0.00343 
C1    1     0.72810  0.70935  0.16881  11.00000  0.01505  0.01775  0.01147 =
 0.00125  0.00226  0.00271 
C2    1     0.59805  0.56270  0.24550  11.00000  0.01268  0.01744  0.01375 =
 0.00217  0.00212  0.00207 
C3    1     0.70810  0.38170  0.24868  11.00000  0.02024  0.01572  0.01899 =
 0.00268  0.00654  0.00429 
C4    1     0.93258  0.47029  0.22986  11.00000  0.01778  0.01907  0.01954 =
 0.00366  0.00454  0.00643 
C5    1     0.59251  0.67779  0.39273  11.00000  0.01718  0.01295  0.01556 =
 0.00538  0.00497  0.00493 
C6    1     0.80835  0.87638  0.60989  11.00000  0.02632  0.01968  0.01502 =
 -0.00005  0.00190  0.00562 
H1    2     1.00699  0.71918  0.13235  11.00000  0.02765 
H3A   2     0.70693  0.33041  0.33541  11.00000  0.03573 
H3B   2     0.62829  0.27590  0.16711  11.00000  0.02631 
H4A   2     1.03778  0.50960  0.32357  11.00000  0.02344 
H4B   2     0.98691  0.36912  0.16881  11.00000  0.02771 
H6A   2     0.74979  0.79311  0.66771  11.00000  0.03635 
H6B   2     0.95992  0.92062  0.64641  11.00000  0.02342 
H6C   2     0.74385  0.99378  0.60034  11.00000  0.02556 

O4    5     0.23967  0.91177  0.08602  11.00000  0.01879  0.02619  0.02446 =
 0.01214  0.00816  0.00637 
H4C   2     0.36203  0.88184  0.10184  11.00000  0.04027 
H4D   2     0.23878  0.98120  0.02012  11.00000  0.04069 
HKLF 4
END
;
